Synthesis and evaluation of novel urea and amide derivatives of 2-amino-4-phenylthiazole as potential antibacterial agents

被引：0
作者：
Zhi-Hua Zhang
Yu Chen
Xin-Jia Yan
Yao Sun
Xiao-Man Yang
Xiao-Yu Cai
Song You
机构：
[1] Shenyang Pharmaceutical University,School of Life Science and Biopharmaceutics
[2] Liaoning University of Technology,School of Chemical and Environmental Engineering
[3] Harbin University of Commerce,College of Pharmacy
[4] Jinzhou Medical University,College of Pharmacy
来源：
Medicinal Chemistry Research | 2017年 / 26卷
关键词：
2-Amino-4-phenylthiazole derivatives; Phenyl thiazolyl urea; Thiazolyl-; -substituted amides; Antibacterial activity;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Two series of novel urea- and amide-functionalized 2,4-disubstituted thiazole derivatives were efficiently synthesized and characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The target compounds were evaluated for their in vitro antibacterial activity against four bacterial strains, including Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa. The results revealed that the thiazolyl-N-substituted amide derivatives 3a–i showed better antibacterial activity compared with those corresponding substituted phenyl thiazolyl urea analogs 4a–i. The compounds 3a–i were particularly active against gram-positive bacteria. Compounds 3f, 3g, and 4g displayed the potent antibacterial activity. Based on structure–activity relationships studies, we observed that the presence of halogen groups such as chloro or fluoro enhanced the antibacterial activity of newly synthesized compounds.
引用
收藏
页码：2080 / 2087
页数：7
相关论文
共 102 条
[1]  
Bharti SK(2010)Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2, 4-disubstituted thiazole ring Eur J Med Chem 45 651-660
[2]  
Nath G(2007)Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp Bioorg Med Chem Lett 17 4635-4640
[3]  
Tilak R(2006)Assessing the nitrogen and carbon nucleophilicities of 2-aminothiazoles through coupling with superelectrophilic 4, 6-dinitrobenzofuroxan J Org Chem 71 5527-5537
[4]  
Singh SK(2004)Phenyl thiazolyl urea and carbamate derivatives as new inhibitors of bacterial cell-wall biosynthesis Bioorg Med Chem Lett 14 235-238
[5]  
Chimenti F(2012)Hybrids of ravuconazole: synthesis and biological evaluation Eur J Med Chem 54 295-302
[6]  
Bizzarri B(2003)Synthesis of some new 2, 4-disubstituted thiazoles as possible antibacterial and anti-inflammatory agents Eur J Med Chem 38 313-318
[7]  
Maccioni E(2008)Synthesis of some novel 2, 4-disubstituted thiazoles as possible antimicrobial agents Eur J Med Chem 43 261-267
[8]  
Secci D(2009)Design, synthesis and biological evaluation of novel thiazole derivatives as potent FabH inhibitors Bioorg Med Chem Lett 19 6750-6754
[9]  
Bolasco A(2012)Synthesis and antimicrobial activities of some isoxazolyl thiazolyl pyrazoles Med Chem Res 21 3541-3548
[10]  
Fioravanti R(2011)Synthesis and antimicrobial activity of amido linked pyrrolyl and pyrazolyl-oxazoles, thiazoles and imidazoles Eur J Med Chem 46 5317-5326
12345678910